This research explores ways of harnessing people?s passion for entertainment in order to stimulate players to attain the meta-learning skills they need for lifelong learning and to reach the highest level of learning, that of learning by teaching. More specifically to keep up with today?s pace of training and the goal for it to be just-in-time, we are interested in creating a game generator to empower grass roots experts to share their stories in such a way that others learn the lessons by engagement and empathy with the storyworld characters. Doing so requires us to address the fundamental issue that caused the entertainment and educational gaming communities to split: that it is not easy to create something fun while constrained by rigid pedagogical goals. We examine a case study of the attempts of one cross-disciplinary team to overcome aesthetic silos, and propose a critical systems methodology and generator that harness the core mechanics that make gaming fun, while providing an accessible means for educators to create content to deliver the educational payload.